It’s About Time You Date Yourself

By. Jaclyn Lupo


February is all about love, and it’s about time we start showing that affection to ourselves. Self-care has been trending for a while now. I’m all about yoga, facemasks, and tea, however, it’s about time we get a little more up close and personal with ourselves. Self-care is all about surface-level relaxation and giving yourself time to breathe. This can help foster self-love, but self-love is much deeper. The beautiful thing is, self-love is like riding a bicycle. Once you create a compassionate relationship with yourself, you will carry those enlightened feelings forever. That’s why it’s about time you date yourself.


What does self-dating look like? Well, for starters, it can simply be taking the time to journal with thought-provoking questions. Whenever you start dating anyone, the first few dates are spent getting your feet wet with your date’s personality and judging whether you want to spend more time with that person. Journaling mimics this process, but instead of a conversation between two people, it’s within your mind. Of course, when you go on your first self-date, it’s going to be uncomfortable. Showing up for yourself with no distractions is not something our society encourages. It may feel selfish to turn off the phone and tune in to you, but let me reassure you, it’s 100% not. You deserve to give yourself time to explore your intrinsic world. After all, don’t you want to discover all there is to know about your beautiful soul?


Some journal prompts to consider for a self-date:

  • What are five things I currently accept about myself?

  • Where am I letting myself play small?

  • What can I thank myself for?

  • What activities/habits/people make me unhappy; how can I let them go?

  • List one thing you’re grateful for each part of your body.

  • What do I deserve?

  • What was a challenge I overcame, and how?

  • If I loved myself, what would I do every day?

Of course, date activities should vary, so as you become more comfortable with the concept of spending time alone, you can start experimenting with the things you do. Try going out for coffee, and instead of scrolling through Instagram, allow yourself to find the confidence to enjoy your own company in public. It’s daunting at first, but over time it becomes second nature. Even better, once you accept that you are capable of anything, independently, you’ll foster more positive emotions towards yourself. You’ll finally be able to appreciate all the beauty you give the world. You’ll understand that you are valuable and worthy of curating a life you are proud of. When you take the time to understand yourself, you’ll figure out what makes you feel content.


In reflection of the past few years, I can wholeheartedly say I would not be in the healthy relationship I am in today if I had not taken the time to date myself. Although my partner and I are currently long-distance (she’s deployed and I’m in college), our level of communication has allowed us to grow despite the 3000 miles of physical distance between us. When I met Caitie, I knew what I needed from a partner since I took the time to sit with my thoughts and evaluate why my ex left me feeling so down. After multiple journaling dates, it became obvious that I felt I was unworthy of *real* love, so I settled for someone who would abuse my good-nature. As Stephan Chobosky wisely says in The Perks of Being a Wallflower “We accept the love we think we deserve.” Oh boy, how that quote speaks the truth. Fortunately, with time, the brain can be trained to acknowledge your true worth. News flash: it’s time you level up from the toxic romances of the past.

Entering the dating scene with a misunderstanding of yourself will only lead to heartbreak and disappointment because you cannot establish what you want from your partner. Heads up, nobody can read your mind. If you don’t like the way he touches you, tell him! If you wish she took you out on more sophisticated dates, tell her! This is your life, and you have every right to speak proudly to your partner about what brings you joy, and what doesn’t. Self-dates will help you gain the confidence to speak up for yourself. You deserve someone who treats you like royalty. Don’t settle, queen.


Today, I challenge you to turn off your phone, grab a pen and a notebook, then simply write. This is a perfect introductory self-date! Write about what happened over the past week. Write about your reactions. Write about your current mood. Let your subconscious drive the pen. After this initial emotional pour, ask yourself, is this the life I want to live? And am I proud of what I’m doing/how I’m spending my time/who I interact with?

If you answer no to any of those, it’s time to dive deep and evaluate what exactly is causing you dissatisfaction. Rome was not built in a day, so allow yourself to spend quality time diving deep into your soul. You’ve gotta go down to your roots to heal so you can learn to grow with love and compassion. Take these findings, and let them drive your journal dates. Let your mind wander. Let yourself explore. And most importantly, let yourself enjoy your presence.


Self-dates will help you find self-love. Self-love will help you find the partner of your dreams if that’s what you want. Have fun getting to know yourself!


Jaclyn Lupo is an editorial writer passionate about fashion, sustainability and culture.

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